KOA - MDW

$269 Find Cheap Flights from Kailua-Kona to Chicago Midway Airport - Compare and Save

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1 adult, Economy, 0 bags

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Everything you should know

Cheapest one-way
$269
Typical prices: $401-$488
Southwest
Sat 2/10
KOA - MDW • 1 stop
Nonstop flights
Not available
There are currently no direct flights between Kailua-Kona and Chicago Midway Airport. You'll need to take a connecting flight to reach the destination.
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Cheap Flights from Kailua-Kona to Midway (KOA-MDW)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Kailua-Kona to Midway

Sun, Nov 29 - Sun, Dec 6
Delta Logo
9:45 pm - 4:39 pmKOA  Kona Intl-MDW Chicago Midway
14h 54m2 stops Seattle/Tacoma Intl Minneapolis St Paul
Delta Logo
6:00 am - 7:55 pmMDW  Chicago Midway-KOA Kona Intl
17h 55m2 stops Atlanta Hartsfield-Jackson Seattle/Tacoma Intl
$938Delta
Sat, Nov 14 - Wed, Nov 18
Southwest Logo
9:30 pm - 1:30 pmKOA  Kona Intl-MDW Chicago Midway
12h 00m1 stop Las Vegas Harry Reid Intl
Southwest Logo
5:50 am - 6:10 pmMDW  Chicago Midway-KOA Kona Intl
16h 20m2 stops Las Vegas Harry Reid Intl Honolulu
$996Southwest
Sat, Nov 14 - Wed, Nov 18
Southwest Logo
9:30 pm - 1:30 pmKOA  Kona Intl-MDW Chicago Midway
12h 00m1 stop Las Vegas Harry Reid Intl
Southwest Logo
5:50 am - 2:00 pmMDW  Chicago Midway-KOA Kona Intl
12h 10m1 stop Las Vegas Harry Reid Intl
$1,086Southwest
Sat, Nov 14 - Wed, Nov 18
Southwest Logo
9:30 pm - 3:15 pmKOA  Kona Intl-MDW Chicago Midway
13h 45m2 stops Las Vegas Harry Reid Intl Denver Intl
Southwest Logo
10:05 am - 9:25 pmMDW  Chicago Midway-KOA Kona Intl
15h 20m2 stops Los Angeles Honolulu
$1,255Southwest
Sun, Nov 29 - Sun, Dec 6
Southwest Logo
11:40 am - 5:40 amKOA  Kona Intl-MDW Chicago Midway
14h 00m2 stops Honolulu Las Vegas Harry Reid Intl
Southwest Logo
5:45 am - 1:40 pmMDW  Chicago Midway-KOA Kona Intl
11h 55m1 stop Las Vegas Harry Reid Intl
$1,312Southwest
Sun, Nov 29 - Sun, Dec 6
Southwest Logo
9:30 pm - 4:30 pmKOA  Kona Intl-MDW Chicago Midway
15h 00m1 stop Las Vegas Harry Reid Intl
Southwest Logo
5:45 am - 1:40 pmMDW  Chicago Midway-KOA Kona Intl
11h 55m1 stop Las Vegas Harry Reid Intl
$1,381Southwest
Booking Insights

Price, demand and travel trends for Kailua-Kona to Chicago Midway Airport flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

Which airline is the cheapest to fly from Kailua-Kona to Chicago Midway Airport?

Delta ($938) and Southwest ($996) are the cheapest airlines to fly round-trip from Kailua-Kona to Chicago Midway Airport according to KAYAK data over the last 5 days.

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Key details for Kailua-Kona to Chicago Midway Airport flights

Cheapest flight

$269
One-way flight from Kailua-Kona to Chicago Midway Airport

When to book flights from Kailua-Kona to Midway

Are your dates flexible? Find out the best times to travel from Kailua-Kona to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Kailua-Kona to Chicago Midway Airport flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What cabin classes can I book on flights from Kailua-Kona to Chicago Midway Airport?

    Only Economy Class is available on flights from Kailua-Kona to Chicago Midway Airport.

  • How long is a flight from Kailua-Kona to Chicago Midway Airport?

    A nonstop flight from Kailua-Kona to Chicago Midway Airport takes 00m, covering 4,213 miles.

  • Do I need a passport to fly from Kailua-Kona to Chicago Midway Airport?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • Have flight prices from Kailua-Kona to Chicago Midway Airport changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route varied from about $938 to $1,381. That means the highest observed fare was about 47% higher than the lowest one.

  • How are flight prices from Kailua-Kona to Chicago Midway Airport looking right now?

    One-way fares from Kailua-Kona to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $380, which is 18% below the typical average for this route.

  • What car rental options are available at Chicago Midway Airport (MDW)?

    Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates averaging $84 for economy cars. Top options include:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

  • Which airports can I use when flying from Kailua-Kona to Chicago Midway Airport?

    Flights from Kailua-Kona to Chicago Midway Airport usually depart from Kona Intl (KOA) and arrive at Chicago Midway (MDW).

  • What is the time difference between Kailua-Kona and Chicago Midway Airport?

    Chicago Midway Airport is 5 hours ahead of Kailua-Kona (Central Time vs Hawaii-Aleutian Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Chicago Midway Airport?

    Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago Midway Airport on KAYAK.

Your guide to booking Kailua-Kona to Chicago Midway Airport flights

Get tips on when to book, when to fly and what to know before your trip.

More options for your flight from Kailua-Kona to Midway

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